A new preparation of methylenecyclopropanes utilizing trimethylsilyldiazomethane

Tetrahedron

Volumn 55, Issue 12, 1999, Pages 3687-3694

  Sakai, Atsushi ^a   Aoyama, Toyohiko ^a   Shioiri, Takayuki ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; ALIPHATIC KETONE; ALKENE; CYCLOHEXENE DERIVATIVE; CYCLOPROPANE DERIVATIVE; DIAZOMETHANE; LITHIUM DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033582996     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01176-4     Document Type: Article

References (20)

1. Reviews: (a) Stang, P. Chem. Rev. 1978, 78, 383.
2. (b) Stang, P. Acc. Chem. Res. 1982, 15, 348.
3. (c) Kirmse, W. Angew. Chem. Int. Ed. Engl. 1997, 36, 1164.
4. (a) Miwa, K.; Aoyama, T.; Shioiri, T. Synlett, 1994, 107.
5. (b) Miwa, K.; Aoyama, T.; Shioiri, T. ibid., 1994, 109.
6. (c) Miwa, K.; Aoyama, T.; Shioiri, T. ibid., 1994, 461.
7. (d) Ogawa, H.; Aoyama, T.; Shioiri, T. ibid., 1994, 757.
8. (e) Ogawa, H.; Aoyama, T.; Shioiri, T. Heterocycles, 1996, 42, 75.
9. (f) Yagi, T.; Aoyama, T.; Shioiri, T. Synlett, 1997, 1063.
10. (g) For a review, see Shioiri, T.; Aoyama, T. J. Synth. Org. Chem. Japan, 1996, 54, 918.
11. The preparation of methylenecyclopropanes from ketones and olefins had already been reported with respect to the study of the intermediate using diethyl (diazomethyl)phosphonate: Gilbert, J.C.; Weerasooriya, U.; Giamalva, D. Tetrahedron Lett. 1979, 49, 4619.
12. The reaction of t-butylmethylketone or diisopropylketone with TMSC(Li)N2 in the presence of cyclohexene gave no desired product.
13. 2, see: Ohira, S.; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun. 1992, 721.
14. 2, see: Ohira, S.; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun. 1992, 721.
15. 2 in the presence of cyclohexene gave the 1,2-rearrangement product (5), 1-phenyl-1-propyne, see ref. 2a. (Table Presented)
16. Gilbert, J. C.; Giamalva, D. H. J. Org. Chem. 1992, 57, 4185.
17. 1H NMR analysis showed the purity of cis- and trans-β-methylstyrene was respectively >98.9%, and each olefin contained its isomer.
18. Shioiri, T.; Aoyama, T.; Mori, S. Org. Synth., Coll. Vol. 8. 1993, 612.
19. McElvain, S. M.; Kundiger, D. Org. Synth., Coll. Vol. 3, 1973, 506.
20. Stang, P. J.; Mangum, M. G.; Fox, D. P.; Haak, P. J. Am. Chem. Soc. 1974, 96, 4562.